期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2020, 期 48, 页码 7429-7434出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202001258
关键词
Quinones; Oxidation; Phytocannabinoids; Iodanes; Tautomerism
资金
- MIUR Italy [PRIN2017, 2017WN73PL]
Spurred by the remarkable biological profile of cannabinoquinoids, we have systematically investigated the periodinane oxidation of their resorcinolic precursors, discovering that the regiochemistry of oxidation, a critical maneuver for bioactivity, depends not only on the nature of the oxidant (lambda(3)- vs. lambda(5)-iodanes), but also on post-oxidative prototropic- and valence tautomeric equilibria that isomerize ortho-quinones to para-quinones. By complementary selection of the periodinane oxidant and by freezing prototropic equilibration with O-methylation, isomeric ortho- and para-quinones could be obtained from mono- and diphenolic cannabinoids, setting the stage for the exploration of novel areas of the biological space, and establishing a blueprint for the extension of this strategy to other classes of bioactive alkylresorcinols.
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